2 files changed, 25 insertions, 3 deletions
diff --git a/src/cryptography/hazmat/backends/openssl/rsa.py b/src/cryptography/hazmat/backends/openssl/rsa.py
index 8bb85783..85d06525 100644
--- a/src/cryptography/hazmat/backends/openssl/rsa.py
+++ b/src/cryptography/hazmat/backends/openssl/rsa.py
@@ -13,6 +13,7 @@ from cryptography.exceptions import (
 from cryptography.hazmat.primitives import hashes
 from cryptography.hazmat.primitives.asymmetric import (
     AsymmetricSignatureContext, AsymmetricVerificationContext, rsa,
+    utils as asym_utils
 )
 from cryptography.hazmat.primitives.asymmetric.padding import (
     AsymmetricPadding, MGF1, OAEP, PKCS1v15, PSS, calculate_max_pss_salt_length
@@ -452,9 +453,18 @@ class _RSAPrivateKey(object):
         padding_enum = _rsa_sig_determine_padding(
             self._backend, self, padding, algorithm
         )
-        hash_ctx = hashes.Hash(algorithm, self._backend)
-        hash_ctx.update(data)
-        data = hash_ctx.finalize()
+        if not isinstance(algorithm, asym_utils.Prehashed):
+            hash_ctx = hashes.Hash(algorithm, self._backend)
+            hash_ctx.update(data)
+            data = hash_ctx.finalize()
+        else:
+            algorithm = algorithm._algorithm
+
+        if len(data) != algorithm.digest_size:
+            raise ValueError(
+                "The provided data must be the same length as the hash "
+                "algorithm's digest size."
+            )
 
         return _rsa_sig_sign(
             self._backend, padding, padding_enum,
diff --git a/src/cryptography/hazmat/primitives/asymmetric/utils.py b/src/cryptography/hazmat/primitives/asymmetric/utils.py
index 5b27654f..44bf59d1 100644
--- a/src/cryptography/hazmat/primitives/asymmetric/utils.py
+++ b/src/cryptography/hazmat/primitives/asymmetric/utils.py
@@ -13,6 +13,7 @@ from pyasn1.type import namedtype, univ
 import six
 
 from cryptography import utils
+from cryptography.hazmat.primitives import hashes
 
 
 class _DSSSigValue(univ.Sequence):
@@ -69,3 +70,14 @@ def encode_dss_signature(r, s):
     sig.setComponentByName('r', r)
     sig.setComponentByName('s', s)
     return encoder.encode(sig)
+
+
+class Prehashed(object):
+    def __init__(self, algorithm):
+        if not isinstance(algorithm, hashes.HashAlgorithm):
+            raise TypeError("Expected instance of HashAlgorithm.")
+
+        self._algorithm = algorithm
+        self._digest_size = algorithm.digest_size
+
+    digest_size = utils.read_only_property("_digest_size")